


Business + Pleasure

by Klaineaholic



Category: Supernatural
Genre: F/M, Fluff and Smut, Spanking, lotsa spanks
Language: English
Status: Completed
Published: 2019-02-20
Updated: 2019-08-01
Packaged: 2019-10-31 22:46:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 9,690
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17858441
Author URL: https://archiveofourown.org/users/Klaineaholic/pseuds/Klaineaholic
Summary: Hunting and sex are never a good mix, in your opinion. But when you find out the handsome stranger you brought home one night is the well-known Dean Winchester, you have to decide if abiding by your principles is worth losing the connection you have with him.





	1. Chapter 1

**Author's Note:**

> This is like... the first reader insert I'd ever written. I like to thing I've improved since then.

_Clink._

Your attention turned to the shot the bartender set in front of you. Raising the shot to your lips, you toasted the bartender and downed the vodka shot, grimacing at the burn that ran down your throat.

You tapped your glass for another; the bartender nodded. While you waited for your next shot, you surveyed the room. Work had been unusually taxing lately, if you could call what you spent most of your week doing ‘work.’ You normally only stopped by this bar when you needed a lay. After the day you had, you definitely needed the sex.

_Clink._

You downed the next shot, shaking your head at the bartender when he signaled for another. You sighed, turning your back to the bar. Yeah, work was mostly doing research for hunters who were passing through or needed help in nearby states. You’d only moved to Arizona recently, after a hunting accident took out an old researcher named Roy who had been in the area for a couple decades. The hunter network had relied a lot on Bobby Singer and a few others, but with Bobby’s passing and the incident with Roy, the remaining researchers were spread thin.

 _Not to mention, I’ve had to go on quite a few hunts recently_ , you scowled. Not that you minded. But there were plenty of hunters and not enough researchers. Unfortunately, you weren’t as helpful to the others if you were out on your own hunts, so you tried to stick to research.

Your eyes went back to scanning the room. You liked this bar because you’d never seen another hunter post up here for the night. You didn’t like to mix work with pleasure, especially since the hunting network was so, well, connected. 

A few prospects were circled up near the dartboard at the back, and several guys were already coupled up on the makeshift dancefloor. Craning your neck, you could see some taller men playing pool near the entrance. A quick glance to your left showed you a drunk and stumbling college-aged kid staggering toward the bar, his glassy eyes catching you momentarily.

_Yech, no thanks. I don’t feel like cleaning up vomit tonight._

You asked the bartender for three shots, and make ‘em quick please. Maneuvering your way through the crowd, you decided the pool table was the closest target and best shot.

“Mind if I grab the next one?” you called out as you set the shots on the high table near the two men. The taller one smiled and stuck out his hand.

“You can take my spot; I’m about done for the night. Name’s Sam.”

“Y/N,” you responded with a grin of your own. Hot mama, I’d like to climb him like a tree. Sam seemed to catch your gaze, but he turned toward the other man who was making his way toward you both.

You turned your attention to him, feeling your gut clench up as you gave him a once-over, and then a twice-over. Your eyes caught his sexy smirk as he strutted around the table, and you felt your face heat up for a moment. He was tall (not as tall as is friend but still tall), he had the brightest green eyes, and the hottest pink lips. Lips that he was licking, and now sucking under his teeth.

You wondered if he’d bite your lips like that when he was kissing you with those soft, pink, cupid’s bow lips.

_Ho-ly fuck._

“Dean, nice to meet ya, sweetheart,” he winked at you. _Definitely a ladies’ man. Definitely getting laid tonight._

“You can call me Y/N,” you shot back with a smirk of your own. Lifting your shot to toast Sam and Dean, you downed it as the men toasted you in return. You waited until Dean’s green eyes were back on you before licking your lips and dragging your teeth over your bottom lip. Dean’s gaze immediately flitted to your tongue before giving you a once-over. He shifted his weight to lean against the table and cleared his throat. Umpf, what a stud.

“Whadya say, Sam, wanna finish gettin’ your ass beat?” Sam shook his head in response, hanging up the pool stick he’d been holding on to.

“Nah, I think I’ll sit back and watch Y/N take you out,” he joked, nudging you with his elbow. You beamed and turned to see Dean’s response, slightly taken aback by how eager he looked at that suggestion. His green eyes lit up with his smile.

You briefly imagined what those bright eyes would look like in your bedroom back home, staring you down, filled with lust and want and –

“Well then, bring it, Y/N!” Dean teased, holding out his stick for you. A chuckle escaped you, and you shook your head as you strode toward the pool table. You racked the balls, intent on drawing Dean’s eyes to your ass while you gathered the sunk balls and lined up the triangle.

_Just because he’s going to be an easy lay doesn’t mean it has to be a boring chase._

Dean briefly wondered if you wanted him to spank you, because you were sure acting like it, walking around and flaunting your ass like that. He watched you, enthralled, while Sam coughed and excused himself to get another drink. Neither of you realized until much later that he never returned to the pool corner.

After you finished setting up, you passed right by Dean on your way toward the cue rack. You let your shoulder brush his, and you could practically feel him undressing you with his eyes. Grabbing your usual cue stick from the rack, you turned and gestured to Dean.

“After you.”

Twenty minutes later and the two of you were neck and neck. Anytime Dean sunk a ball, you sunk one. If you missed, he missed too. The past few minutes had been slow and torturous, both of you struggling to get in your last shots. _Although_ , you thought smugly, _Dean’s missing his because he’s distracted and I’m missing mine because of poor form._ By poor form you mean, of course, sticking out your ass as you leaned over the table in order to keep Dean distracted.

Dean missed his next shot, but it was most certainly not because you were sweeping your hair back into a ponytail. He briefly imagined you asking him to tug on that ponytail while he fucked you from behind. Shaking his head, he wrapped his lips around his beer and finished it off.

Distracted as he was, Dean was well-aware of what you were doing. And he wasn’t one to be out-played. On your next turn as you were bent over the table, he disappeared from your line of sight and reappeared pressed up behind you; his arms framing yours and tweaking your hold on the cue stick, his hips pressed against you, his deep voice and hot breath reverberating in your ear.

“Here ya go, sweetheart.” His fingers wrapped around yours on the cue stick. “Don’ wanna grab too tight now.” You immediately felt your brain cloud up as your breathing shallowed. Adjusting your grip, you followed Dean’s lead. You made the shot.

“I win,” you whispered; Dean hadn’t moved, his warm breath still fanned over your cheek, leaving a growing blush in its wake. You closed your eyes, trying to clear away some of the fog from your brain and the heat from your face. You slowly moved against Dean, indicating you wanted to stand up straight; he reluctantly moved with you. His arms dropped from your arms to your waist, and you felt his thumbs circle around the exposed skin above your jeans.

Turning your head back to see him, you felt his lips near your ear again. “Wanna get outta here?” he whispered, his voice thick and gravelly and low.

“Thought you’d never ask,” you breathed out. For a second, neither of you moved. Dean muttered something about paying his tab and letting Sam know he was heading out. As soon as he moved away, you felt his heat go with him.

Not even two minutes later, Dean met you outside where you went to wait and cool off in the fresh air. You were leaning against the wall of the bar, chewing on a thumb nail while you waited. Dean slid in front of you, leaning against the wall on one arm, the other dancing at your waist. Your eyes met his, green and dark and heavy with want.

You leaned up, wrapping your right arm around his neck and dragging your left hand through his short hair, not wanting to wait for Dean to make the first move. Your lips met his, and you could feel your pussy becoming wetter by the second. He was slow and gentle, but definitely in control. His teeth dragged on your bottom lip, and as you opened your mouth to gasp, his tongue slid in to meet yours. Then he was kissing the corners of your mouth, your jawline, your ear, then ahh!

You moaned high and breathy, fingers grabbing at his hair as his lips connected with the dip behind your jaw, right under your earlobe. You felt his lips smirk as he nipped that same spot, immediately kissing and lightly licking it afterwards.

“Dean,” your voice cracked, again sounding higher than your normal tone. Your skin was on fire, and you could feel his hand sliding around your waist underneath your top. If you stood here much longer, you were worried you’d undress each other right under the street light.

“Yeah darlin’?” Dean offered, resuming his work and now moving further down your neck.

“Home. Uhhh. Bed. Two blocks ahhh!-away,” you stammered out. Dean pulled away, changed his mind and came back in for a deep kiss, one where his lips moved perfectly against yours, where your knees grew weak, and your noses brushed the other’s gently. He finally pulled back, letting the arm from your waist trail down your forearm, his fingers slipping between yours. “Lead the way, Y/N.”

The walk took five minutes, but you made small talk. You mentioned how the city didn’t really feel like a city since you were closer to the outskirts. The bar you had both left wasn’t as popular because of its location away from the middle of the city, but it received enough business from the other patrons who didn’t want to venture toward the college bars and clubs downtown.

As you jiggled your key into the door, Dean’s hands slid back to your waist, his lips sneaking up behind your ear and planting kisses as you giggled and pretended to brush him off. Suddenly you were both in the house and the front door was locked again; you were wrapped around Dean’s neck again, lips colliding with his again, his hands circling your hips again.

You pulled away (reluctantly) and pulled him toward your room, which was off to the right on the main level. Once you were in the room, Dean whirled you around to face him. His green, lust-filled eyes looked you up and down and his large, calloused hands lifted your shirt up and off. He traced the shape of your bra, causing you to skip a breath or two. You reached back to unclasp it, but his hand snatched your wrist, holding it down by your side. His other head reached around, fingers moving quickly to snap it open. Both hands traced the straps, gently guiding them down your shoulders.

“Gorgeous,” he breathed, thumbs flicking over your hardening nipples. Your eyes rolled back, your mouth dropped open in a gasping moan as he repeated the action again, and again, and again –

You felt his hands drop to your jeans, fiddling with the button and zipper. He tugged, leaving your panties untouched and increasingly more soaked. You helped him work the jeans down and kicked them and your shoes off your feet. Dean took a step beck, hand palming his cock through his jeans, his eyes scanning over you ravenously.

“Y/N, jeez. Holy shit.”

“You’re stripping too right?” you teased, eager to move faster, but relishing the teasing pace Dean had set. Dean let out a laugh, the corners of his eyes crinkling with his smile. He pulled off the button up, reaching behind his head to tug off his t-shirt. You let your eyes examine his muscled torso as much as you were able in the dark room, very much appreciating his build. He kicked off his boots, sliding so smoothly out of the denim. You let out a groan at his cocky, bowleg stance and at his cock, very clearly pressing against the confines of his boxer briefs.

“Turn around and take ‘em off, sweetheart,” Dean nodded at your panties. “Slow.”

A fresh wave of arousal hit you; Dean wanted to watch you bend over for him again, like you did at the bar over the pool table. Only this time you’d be naked. You turned, tucking your thumbs in the waistband, slowly dragging them front to back, inching your soaked panties down to the floor. You started to straighten up when you heard Dean groan.

“Wait,” his voiced cracked. “Hands on the bed, sweetheart.”

Your face was hot as you adjusted your position, legs spread a little wider to accommodate your leaning, back arching slightly; Dean’s hand traced along your spine, down to the globe of one cheek, under, and around the other. His touch was feather light, leaving goosebumps trailing behind. Your ass involuntarily jutted out toward him. He groaned again, palming one of your ass cheeks and rubbing it gently.

“You like it a little rough, Y/N?” he asked. “Jus’ say th’ word if you don’t.”

“God, yes,” you moaned. His hand left your ass.

_SMACK!_

“Ahhhh!” you gasped as the sting of Dean’s hand met your ass. He was rubbing it gently again, groaning and muttering beautiful, filthy words of encouragement.

“There ya go, you like that, don’tcha? Such a pretty, perky ass. Wanted to smack it so many times while you were bendin’ over that pool table back at the bar.”

_SMACK!_

You let out a short scream as Dean’s hand connected again. Instantly his hands were back on both cheeks, rubbing softly, slowly. You felt him move behind you, felt his hot breath near your ass, felt his lips peppering kisses on each cheek. Your head was clouded, eyes rolling back when he bit your right cheek.

You jolted, forward at first in shock, and then back toward him in pleasure. “Dean!”

As one hand rubbed your left cheek, he nipped your right cheek again; his right hand left a blazing trail as it crept up between your legs, caressing each inner thigh, until he stroked you from your clit back towards him, dipping inside you. You let out an _ahhh!_ and shuddered, falling from your hands to your elbows on the bed, your ass sticking out just a bit more. Dean continued just a few moments longer, stroking, nipping and biting your ass, and then dragging one of his long calloused digits across your soaking entrance.

“So wet, so ready for me, beautiful. That’s right, sweetheart,” he murmured. He pulled away slowly; first his wandering hand, then his mouth, and finally his other hand stroked across both cheeks and pulled away. You whined at the loss, thrusting your hips back toward him hoping to connect. He chuckled, swatting at the side of your ass and earning a low moan from you.

“Lay on your back for me, will ya, Y/N?”

Once you had rolled over and situated yourself on the king-sized bed, legs hanging over the side, your head and chest propped up as you sat up on your elbows, you watched as Dean tugged off his underwear. Your mouth dried up and you desperately licked your lips. Dean’s long, thick cock had sprung free from its cloth prison, bounced a little, and was jutting out at you.

Dean caught your eyes and let a grin slide over his face. He stepped forward and kneeled in between your legs, letting each of his hands rest on your inner thighs. He pushed them open a little more, leaning in to smell you. You whined, threw your head back and your arms out, and tried to move your legs, your hips, but Dean pulled away.

“Now, now!” his grip on your thighs tightened. “Y/N, look at me.”

You rolled your head around with an _ooh!_ , making eye contact with Dean and his deep green eyes. You decided then and there that Dean would never leave your house. You had barely been undressed and he had you more worked up than you could ever remember being. And his eyes – green and dark, but still playful; they were a treat to get lost in.

“Y/N, I’m gonna eat your pussy,” he said it so nonchalantly as he stroked your thighs, like he had just declared it was going to rain tomorrow. You gulped and nodded.

“Gonna make you feel so good, Y/N, so relax. Got it?”

Your head rolled back, your brain clouding up again. You felt a sharp nip on your inner thigh, and a pant escaped you.

“I said, ‘got it?’” Dean growled playfully, lips pressed up against your thigh, kissing where he had just nipped at you.

“Yeah-uh, uh-huh – yes,” you stuttered out. Dean’s nose was pressed up against your clit in seconds, his lips and his tongue exploring the outer folds of your wet pussy. He released one of your thighs, trailing his thumb gently around your clit as he shifted his tongue into your entrance. You felt yourself building up, and then Dean’s lips were on your clit, his tongue pressing hard against it, and he had two fingers fucking up into you slowly. Your moans grew louder as you shook and whined and pulled at Dean’s hair, praying he would never leave, never stop eating your cunt.

His tongue on your clit brought you to orgasm more quickly than you anticipated; it left you shuddering and shaking, as he ran his hands over your legs, your stomach, and around your hips. He had been riding with you through your waves of pleasure, but you quickly realized once they settled, he hadn’t, and he wasn’t planning on it.

You gripped Dean’s head, stroking his hair as he gently licked your clit and planted kisses around your folds. It was pleasant, and soon you felt new arousal building up within your core. This time, Dean was much slower, teasing you, edging you closer to orgasm and then pulling away to kiss your thighs and stomach before returning his gentle mouth to your cunt.

You were begging, practically wailing for him to let you come when suddenly his hands grasped your hips tightly, pulling you in closer as he furiously sucked and licked at your clit. Your orgasm crashed in again, and you had to pull your knees up and drag your fingers through Dean’s hair to ride it out.

Dean pulled away once you stopped twitching, his chin glistening with you. He crawled up the bed and lowered his mouth to one of your nipples. He licked gently, mouthing your breast and letting his teeth gently brush against your skin.

“Harder,” you whimpered as you writhed beneath him, one hand holding his head down and the other scratching across his back. Dean obliged, putting more pressure in his nips and bites as he jumped from one nipple to the other. His spare hand trailed down your torso and he slipped a few fingers inside of you, fucking his fingers into you quickly, eliciting a gasp and some breathy fucks from you.

You wrapped yourself around him, arms encircling his head and shoulders, legs wrapping around his waist, and a few minutes later you came again. Dean pulled his fingers out, licking them clean, grinning down at you.

“Fuck, Y/N. You taste so good ‘n’ you come so good for me, sweetheart,” he whispered against your neck and lips as he kissed you over and over again, letting you taste yourself on his lips.

“Dean, I need you. Now,” you sighed as you reached for his hips to drag him closer. Dean shifted, then stood.

“On your hands and knees sweetheart. Face that headboard for me,” he encouraged you. You nodded and moved as quickly as your spent legs allowed to get into position. You could see Dean searching for his jeans to your right.

“Condoms in the drawer, Dean.”

He was there in an instant and then behind you, sliding the condom on and lining up his cock with your cunt. He groaned.

“Your ass makes sucha pretty picture, Y/N. Yeah, arch that back too,” he grabbed your hip and started to slide his cock into you.

“Jeez, holy fuck, Dean!” you cried out. He filled you up so well, and you could hear him making sounds too as he slid right in. “Feels so good,” you whimpered as you reached for the headboard. Dean filled you to the brim, his hips flush against your ass.

“Shit, fuck, sweetheart,” leaving one hand on your hip as he started to slowly rock in and out of you, he let the other trail up your back and wrap around your ponytail. He tugged, gently at first, and upon hearing you sigh, he tugged harder with the thrust of his cock.

The nerves down your neck tingled as Dean tugged your hair, timing his pulls with the thrust of his cock, your breath catching in your throat as you tried to moan. Dean could feel you tightening around him and he slowed his thrusts, moving your hips to turn you to your back again. He settled above you and pushed into you again; you wrapped your legs around his hips and your arm around his back, trying to pull him deeper, deeper, harder.

Soon, Dean’s thrusts were getting erratic, and you could feel your fourth wave of pleasure reaching its breaking point. Your hands grabbed Dean’s head, fingers threading through his hair. You made eye contact with him and whispered, “Come with me, Dean!”

Dean held your gaze and a few thrusts later, you both broke eye contact as Dean grunted ‘Fuck, Y/N!’ and you screamed ‘Dean!’ You clenched around him as he swelled up, and he thrusted a few more times, burying his head in the crook of your neck. You were both panting, trying to catch your breath; Dean was still inside you, softening very slowly, and you were still wrapped around him tight. He lifted his head, satisfied smile spreading across his face as he leaned down to kiss your lips. You _mmm_ ’d happily, giggling when he kissed your forehead before pulling out of you with a _squelch_ from your juices.

You rolled over to the side of the bed, debating on your need to pee and how long you could stand up at the moment without falling over. Dean seemed to be contemplating the same thing.

“Ah, I have a guest bathroom out in the hall,” you gestured as you made to stand and head toward your ensuite bathroom. “To the right and a couple doors down.”

“Thanks darlin’,” Dean drawled as he stood and slid off the condom. Making sure he didn’t leave behind a mess, he hustled down the hall to clean up.

Once you made it back to the room, Dean was waiting for you on the bed in his boxer briefs. You smirked.

“You tryin’ to be a gentleman, or do you think I’m gonna cook you breakfast in the mornin’?” you teased as you dug through a drawer for pajamas.

“I don’t see why I can’t help make breakfast, but I can head out if you want,” Dean offered cheekily. He sneaked up behind you and wrapped his firm arms around your waist, nuzzling your neck. “Was kinda hoping for a round two, but I understand if you can’t take anymore.”

You gave him a mock gasp, “How dare you! I’ll have you know, my libido is quite high and healthy, thank you very much.”

Dean chuckled; it was low and throaty and deep and God you wanted to fuck him all over again. “I’ll be the judge of that.”

He whirled you around and lifted you up, your legs and arms wrapped around him once more as he carried you into the bathroom.


	2. Chapter 2

Waking up the next morning was a slow process. You were groggy, but felt warm and satisfied. You shifted, straightening your legs from being curled up most of the night. The backs of your knees bumped something warm and firm. You let out a wordless protest and tried to turn and see what your knees hit.

Your torso was held in place by another firm, warm thing. As you blearily blinked your eyes open, you saw a man sleeping soundly behind you and his muscled arm holding on to you by the waist.

_Dean_.

The events from last night spun around in your head. The attractive man had walked home with you from the bar and had, to be frank, fucked you down to hell and back up again.

And he had stayed. You mulled it over in your head for a moment, before letting a smile creep across your lips. Well it’s not like it’s anything long-term, but it’s sweet.

Eyes scanning over Dean’s freckled face and shoulder, you decided to stay right where you were and enjoy yourself for the time being. As you laid your head back on the pillow, you readjusted, placing your hand over Dean’s and pressing yourself a little closer to him.

You felt his chest rumble against your back with his own sleepy groan as he pressed his face to the crook of your neck. He hmm’ed happily, palming your hips so he could prod his morning wood against your ass. You let out a chuckle, and Dean peppered your neck and shoulder with kisses.

“Well good morning,” you greeted him with a wiggle of your ass.

“You bet your ass it is,” he responded as he ran his hand over the aforementioned bum.

You laughed just as a phone in the room started going off, buzzing against the floor and playing a hard rock ringtone. Dean grumbled and held on to you a second longer.

“T’s Sammy wonderin’ where I’m at,” he explained as he rolled away to answer his phone. You turned to sit up in bed, admiring Dean’s broad shoulders, muscled back, and his very nice ass while he shuffled through the mess of clothes on the floor looking for his phone. He answered the phone with an exasperated _what?!_ and began pulling on his boxer briefs.

He pointed out your door and mouthed _bathroom_ ; you nodded in response as he shot you an apologetic smile and left the room. You let out a resigned huff, and crawled out of bed to pull on some clean underwear and Dean’s shirt.

After swinging by your en-suite bathroom to brush your teeth and check your hair, you decided to go start breakfast just in case your morning with Dean was cut short. Straight out of your room was the entry and living space, and to your right was a short hallway with the doors to the other bathroom two doors down on your right and library full of lore on the left. Choosing to give Dean some privacy, you went through the living room to get to the kitchen.

You were just starting to cook the bacon and eggs as you heard Dean open the door from the bathroom.

“I’m in the kitchen,” you called over your shoulder.

A few minutes later, you heard footsteps behind you and felt Dean’s arms snake around your waist. He rested his chin on your shoulder and you could hear the smile in his voice as he spoke, “Bacon! I knew I smelled breakfast.”

You chuckled, “Wanna get the toast ready? Bread is in the basket by the fridge. I don’t have coffee, but I have chocolate milk and orange juice if you want to grab a couple glasses too, second cabinet to the left.”

“No, coffee?!” you heard Dean scoff under his breath. As he popped the bread in the toaster and located the glasses, he began speaking.

“That was Sam, he’s gonna swing by in an couple hours and scoop me up. We gotta meet up with a family friend in town.” He strode over and tilted your chin, pressing a quick kiss to your lips. “I’ll be in town for another week or so. Maybe we can…?” He trailed off with a pseudo-cocky grin. You let the idea float around in your head a little.

Even if he just wants to fuck some more, he is a fantastic lay. Besides, he’s just passing through.

You nudged him with your elbow and asked teasingly, “You trying to woo me, Dean?”

He chuckled and gave you a wink, “Sweetheart, I’d be crazy not to try.”

One of your hunter lines from the library started to ring. “Shit, can you watch the eggs?”

You ran off to the library and, hands skimming over the assorted labeled phones on your wall and desk, you snatched up the right phone before the final ring.

“Y/L/N, what’s up,” you huffed as you tried to catch your breath.

“Y/L/N, it’s Tara. You should have some reinforcements coming up for that Wendigo up in Hells Canyon. I spread the word about it earlier this week and just heard back from Irv that the Winchesters were heading your way.”

“Thanks, Tara, I’ll keep an eye out for them. Do they have my address or phone number?”

“No idea, I’ll have Irv shoot them a text. I’m not trying get in touch with any Winchester, and you’d be smart to keep their visit short,” Tara scoffed. You let out a harsh ha!, thanking Tara for the information. You were close enough to her to know she had once hunted with John Winchester, but you’d never met him or his sons. From Tara’s stories, John had been a ladies’ man, and she had never forgiven him, or his kids, for it.

You swung back by your room to grab your phone and met up with Dean in the kitchen. Leaning on the doorframe, you watched Dean standing in his underwear, plating the bacon, eggs, and toast. He poured orange juice and chocolate milk into two separate glasses, and began searching the drawers for silverware. You watched as he set the table and began searching the cabinets.

“Over here, handsome,” you called out. Dean turned, licked his lips as he looked you up and down. He left the cabinet open and strolled over to you.

“I was lookin’ for salt and pepper for th’ eggs, but sugar is close enough,” he quipped. You reached up and patted him on the cheek.

“You are funny. Maybe I will keep you around,” you joked. You collected the salt and pepper and joined Dean at your tiny kitchen table, knees knocking gently against his, his fingers brushing over your knuckles while the two of you ate. You and Dean joked around, talking about Dean’s job as a mechanic, your cover job at the library (“Surrounded by nerds!” Dean joked as you cuffed him playfully), and your life in the city.

“So, what you spend all day reading?” Dean asked as he tried to tease you again about your job. You chucked, if he only knew.

“Not all day, and besides, it’s interesting stuff. I fight a little too,” you countered half-truthfully.

“What kinda fighting?” Dean asked, his eyebrows raised in interest. You shrugged.

“Mostly krav maga, but I know a little about mixed martial arts.” You smirked. “I could probably knock you on your ass, to be honest, but I kinda like you.”

Dean scoffed.

“Besides,” you retorted, “don’t you spend all day under a car or in it?”

Dean opened his mouth to defend himself, but he couldn’t seem to find the words. You laughed as he reached over to tickle your waist.

“Oh you think you’re funny now, huh?”

Breakfast was over before you knew it; Dean helped you clear away the table. With him washing the dishes and bumping you with his elbow and hips while you dried them, cleaning up soon turned to Dean pulling you in front of him, kissing your neck, lifting you onto the counter and running his soapy fingertips down your bare legs.

“Mmm.. Dean,” you whispered between kisses. “How much time until Sam-“

“He can wait,” Dean growled as he tucked his hands under your ass and lifted you off the counter. You held on tight, arms wrapped around his neck and legs enveloping his hips. He made it as far as the living room before neither of you could wait any longer; Dean laid you on the couch and pulled off his underwear.

“No,” Dean said as you began to pull his shirt off of you. “Leave it. It looks good on you.”

He kneeled on the couch, pulling off your panties and tossing them over his shoulder. He leaned over, barely fitting on the couch himself, and immediately drew his lips around your clit and sucked hard. You jolted up with a breathless scream. Dean glanced up at you, ran his tongue around your clit and down into your soaked pussy. You fell back, shoving your hips up to meet Dean’s tongue thrusting into you.

His hands grasped your hips, holding them down firmly as he continued to fuck you with his tongue. As you felt your orgasm building up, he slowly pulled away, his pink, cupid’s bow lips leaving kisses around your inner thighs.

“You stay put,” he grinned as you whined. You watched as he ran off in the direction of your room, his hard dick bouncing a little with each step. You heard him shuffling for a while in your bedside drawer looking for condoms. You frowned. The condoms are right there, what is he looking-

The shuffling stopped and Dean re-entered the room seconds later. He held a wrapped condom in one hand and in the other –

“How the hell did you find my vibrator?!” you yelped. Dean’s smirk grew even wider.

“Thought I saw it rollin’ ‘round in your drawer when I was looking for condoms last night. Figured I’d try it out, if you want.”

You grinned and rolled your eyes. “Of course I want, now get your ass over here.”

Dean kneeled on the couch again, your legs spread on either side of him as he turned on the vibrator and ran it around your mound, inner thighs, and just over the lips of your pussy. He reduced you to moans and _oohs_ and _aahs_ as he drew the toy up and down your lips, teasing as he began to slide it in before pulling it right back out. Finally, Dean slipped the vibrator in and when the clitoral stimulator on your vibrator met your clit, you threw your head back, gasping and yelling in pleasure as Dean messed with the buttons and increased the speed of the vibrations. He dragged it in and out of your pussy, painstakingly slow and then unbearably fast. You were shaking already when he began to stroke every part of you that he could reach with his free hand.

“Fuck, that’s it, Y/N. You look so good, gonna look so pretty coming for me.”

You could feel your orgasm building inside you, pulsing, rushing, climbing –

“Ahhhh!” you screamed, fists clenched and eyes squeezing shut as you came, orgasm crashing through you in waves. You lied still, eyes shut and legs twitching a little, trying to catch your breath.

“Woah,” Dean whispered. You cracked your eyes open, gaping in surprise at the sight between your thighs. You had squirted all over the vibrator, Dean’s hand, and the couch. Even the head of Dean’s cock was covered with your come. Your face was flushed as Dean set the vibrator aside and grabbed the condom, rolling it over his cock.

“So hot, you know that?” he muttered as he leaned over you, easily sliding into your soaked pussy. You moaned, Dean covered your mouth with his, kissing your lips then your neck then your jaw. “So beautiful, perfect, fuck!”

Dean’s thrusts had quickened, and he paused for a moment, grasping your ankles and setting them on his shoulders. He leaned over you further, the angle pushing him deeper inside you.

“Fuck, Dean, jeez,” you gasped. Your hands grabbed at his neck, trying to pull him as close as your flexibility allowed.

Still sensitive from your first orgasm, you were quickly approaching your second, muscles clenching around Dean’s cock. He groaned, slowing down and easing out of you again. You protested with a groan.

Dean pulled you up. “Not yet, wanna see you on top o’ me, sweetheart.” Once he was in a sitting position, you mounted him, sliding him up into you. Resting your hands on his shoulder, you eased all the way down. Dean tightly clutched your hips, grinding you down on his cock as he thrusted up into you. Your hands moved from Dean’s shoulders up to the sides of his face, fingers running through his hair as you rested your forehead against his.

Dean’s green, magical eyes met yours and your breath caught in your throat. His breathing seemed to stop too, or at least slow down. His hands moved up under the shirt you were wearing, and he brushed his fingers against your waist, around your breasts, and across your nipples as his thrusts slowed. You were leisurely moving above him, rotating your hips, nose brushing his.

Your eyes watched Dean’s pupils dilate, his green irises slowly being overtaken by black. You were moving together, breathing together, seeing each other together.

Dean tilted his head, eyes drifting shut as his lips met yours. He sucked on your bottom lip, nibbling gently. You kissed him back, letting his tongue slip in and right back out, steadily sliding up and down over him. He pulled away and locked eyes with you again.

“Y/N.”

“Dean.”

Dean tensed and sped up his thrusting, and you caught the hint. Slipping your hands back down to Dean’s shoulders, you used him to steady yourself and fuck down on him faster. You felt Dean swell inside you just as you began to constrict around him.

Dean’s thrusts became sporadic and your head fell to his shoulder as you both came, Dean with a deep grunt, you with a scream. You both were breathing heavily, staying still for a minute, before you pulled your head up, kissed Dean, and climbed off of him.

Dean’s lips were wide in a half smile, half smirk. “Not bad, heh?”

You snorted while you peeled his shirt off of yourself and threw it at him in a half-formed ball. “Not bad? Enjoy smelling like my sweat and sex around Sam,” you retorted with a smirk.

“Ooh, I plan on it,” Dean laughed as he peeled off the condom.

You tossed your hair up and made your way to the bathroom, hopping in the shower to rinse off the sex and sweat. Dean slid in just as you were finishing up, his hands drifting over your breasts, tempting you to stay for another round.

But Sam would be by any minute to pick up Dean and you had to prep for the Wendigo hunt that the Winchesters were coming in for. Besides, he’s in town all week. You stepped out of the shower (already regretting your responsible decision), dried off and got dressed.

Dean finished his shower soon after, and as he tied off the last knot on his shoes, you both hear the rumble of a car engine outside. Dean beat you to the door, motioning for you to come see, Baby. You followed him outside, seeing Sam standing by a sexy, black Impala. Sam had his phone out, his eyes darting around and glancing from the phone, to your house, to Dean, and then to you.

“Y/N, you remember Sam, and this,” he said gesturing to the Impala, “is Baby. Sam, you remember Y/N. Sam? What’sa matter, Sammy?” Dean asked as he stood on the sidewalk between you and Sam.

“Uh Dean? This is the address Irv sent me. For our… uh… friend? Y/L/N?” Sam stuttered out.

“Wait, Irv?” you interrupted before Dean could open his mouth. “Irv Franklin?”

Sam nodded with a yeah as Dean looked back at you. Your brain was running 70 miles an hour as you met Dean’s confused stare.

“Dean. What’s your last name?”

“Winchester, why what the hell’s goin’ on with you two?” Dean asked exasperated.

“Y/N Y/L/N. I’m a hunter,” you said flatly. You huffed in amazement as Dean’s jaw dropped in shock. “And apparently, so are you two.”


	3. Chapter 3

A wave of panic had washed over you, but now were fuming. A hunter?! You had slept with a goddamned hunter.

“Dean, I need to speak with you inside,” you demanded stiffly, heart pounding in your ears as you tried to prevent your embarrassment from showing on your face.

You stormed back into the house, not waiting for Dean to respond. He turned to Sam and gave him a bewildered shrug before following you inside.

As soon as the front door was shut, you whirled around on him. Taking in his face (why is he so fucking attractive?!) you swallowed down the lump in your throat. You choked out, “This was a mistake.”

Hurt flashed across Dean’s face momentarily, and a pang of regret shot through your heart.

“Huh, really,” Dean snorted. It wasn’t a question.

“Yes really, Dean,” you countered. He stared you down with a raised eyebrow and an otherwise neutral expression, and took a step toward you. Heart thumping wildly, and nerves tickling through your fingertips, you took a stuttering step backward.

Steeling yourself and puffing out your chest, you objected, “Dean, we’re going to be working together. If you think sleeping and hunting together is a good idea when we barely even know each other, you’re sorely mistaken.”

Dean let out a chuckle, “Why’s that sweetheart? You gonna be distracted if I’m on a hunt with you?”

“No!” you answered too quickly. Dean raised an eyebrow in amusement. 

Huffing in frustration you continued, “I just mean there’s monsters out there who will take advantage of that. I’ve seen vamps smell that shit out in seconds and use it to their advantage. It’s dangerous. Not to mention –” you paused, furrowing your eyebrows before continuing your rant, “Listen you’re really great, honestly. But I’m not looking for a relationship. I’ve only been a hunter for a couple years, but I’ve seen what happens who you lose someone like that to this life.”

Dean studied you, maintaining eye contact with his (goddamn it they’re beautiful) green eyes that sucked you in. Like a predator, he approached you, calm and steady and confident. Another argument rose in your throat and faltered as Dean backed you against a wall. He hadn’t touched you, and you almost wanted to whine for him. Fuck, keep it together Y/N.

Forearm resting on the wall above your head, Dean towered over you, easily taking your breath away.

“Ya’see, Y/N,” Dean drawled. “Way I see it, we’d be helping each other out quite a bit.” His warm breath tickled your face, and you forced your breathing to continue uninterrupted.

“Your first argument would be understandable for any other hunter,” he started, letting his free hand brush strands of your hair behind your ear. “But fortunately for you, this is me we’re talkin’ ‘bout here. I got more years under my belt than most hunters I know. Those sons’a bitches don’t stand a chance.”

His thumb brushed your cheek gently, tracing your jawline, voice rumbling through you making your head dizzy. “Second, I’ll be damned if I let anything happen to you. And if you know anything about me, I’m good on my word.”

Fuzzy and foggy from arousal, you were inclined to agree with him. He was a Winchester for fuck’s sake. From the rumors, they’d died and come back for each other more times than anyone would think possible.

“Now I don’t know about you,” Dean muttered, as he tilted your chin and leaned in. “But I’d like to give it a shot and see where it goes.”

You chewed on your lip, eyes flickering between Dean’s. His tongue flicked out, wetting his lips before he leaned in to kiss you.

You had a sudden moment of clarity; dodging Dean’s lips (later, hopefully- no definitely later), you slid under his arm and away from his hypnotic eyes. Dean turned to you, and you could see he was befuddled and slightly frustrated by the way his hand dropped from the wall and twitched at his side.

“We have a Wendigo to hunt,” you declared unwaveringly. “Afterwards, we’ll see.”

A smug smile spread across Dean’s face, and he winked, “’We’ll see’ just means yes, but later.”

You shrugged, met his smile with your own, and moved toward the front door to invite Sam in.

You filled in the boys on the Wendigo sightings, trying to focus completely on the job. Sam and Dean weren’t making it easy. Sam kept looking between you and Dean, giving each of you odd looks. Dean was, well, himself. He was focused, sharp, asking questions about the victims and the time of day they went missing, and damn he looks good doing it.

After a few minutes of back-and-forth, Dean glanced over to Sam. “Sounds like more than one Wendigo to me, eh Sammy?”

Sam agreed as you turned to Dean in confusion. “Why not just one?”

“Two vics visited Hells Canyon last week on the same day, but were both found that night dozens of miles apart, time of death estimated within the same hour. Wendigos are fast, but not that fast. There’s no way only one o’ those bitches got both vics with how far apart they were,” Dean explained, glancing over to Sam for confirmation.

You gazed at Dean in awe as he and Sam were caught up in discussion, fairly impressed with how quickly he came to that conclusion. I guess that’s what more than my two measly years of hunting gets you.

He caught your eyes and offered up a smile. The three of you searched your weapons supply for flamethrowers, then piled into the Impala (Dean winked at you through the rearview mirror from his spot in the driver’s seat), and drove off toward Hells Canyon.

The job itself didn’t take too long; most of the time was spent hiking to the area where the bodies were found. Sam had suggested splitting up so you started walking ahead with him, ignoring Dean’s eyes on your back. You didn’t need to be distracted on this hunt, and neither did he.

About a two hours into your search, Dean had burned one Wendigo to a crisp, and he was circling back to meet up with you and Sam. Hearing the shrieking of the other Wendigo up ahead, he rushed up and around the corner, finally catching up to you and Sam. He gaped in awe as he took in the scene before him. Sam was lying on the ground several feet behind you, holding onto a bleeding arm. And you, you were a vision. You had the flamethrower aimed toward the Wendigo, flames whirling around it, the light casting a long shadow of your silhouette over the ground.

Dean couldn’t take his eyes off you. Your hair was whipping around, legs and arms braced and shining with sweat as the flamethrower in your hands blasted fire at the screeching monster. You looked like a goddess wreaking havoc in your wake.

When the Wendigo was reduced to ashes, you turned around, slinging the flamethrower over your shoulder by its strap. You were covered in a thin layer of sweat, ashes from the monster sticking to your clothes and face. Dean was in awe, and it took him a few seconds to snap out of it.

You were already crouching in front of Sam, checking on his arm. Dean approached you both, eyes raking over you before he turned to his brother, helping him stand. Sam was brushing Dean off, insisting he was fine. You observed Dean’s face as Sammy told him about the Wendigo catching him off guard, knocking him over, and slashing open his arm.

His gaze flickered to you and the corner of his lip quirked up when Sam spoke about you jumping in front of him, turning the flamethrower on the Wendigo, and forcing it away from him. You swelled with pride. You had not only saved one Winchester’s ass, you’d also earned some serious respect from the elder Winchester.

After wrapping scraps of Sam’s fleece around his wounds, the three of you worked your way back to the Impala, with the sun beginning to rise on the horizon.

Once you reached Baby, Sam insisted on lying down in the back, wanting to rest until he could get stitched back up at your place. While he crawled into the backseat, Dean tugged at your wrist and pulled you aside. “Listen, Y/N, thanks for having Sam’s back out there. I owe you.”

“Sure, it’s what we do, right?” you smiled and shrugged. Eyes twinkling, Dean offered up a half-smile in return and pulled you into a hug, pressing a kiss to the top of your head. He smelled like ashes and sweat and he was warm, solid, inviting. You tentatively wrapped your arms around him, resting your head against his chest.

“You thank all your hunter friends like this?” you asked jokingly. Dean huffed and gave one last squeeze before releasing you. He held open the car door, letting you slide into Baby’s passenger seat before closing the door. You heard Sam chuckle from the backseat.

“What’re you laughing at, Winchester?”

Sam muttered, “He likes you a lot, you know. You should give him a chance.”

Your breath hitched, and before you could respond, Dean’s door opened. Your eyes caught his momentarily as you both buckled up. Turning away, you looked straight out the windshield and spent the remainder of the drive catching Dean’s periodic glances and returning them when he wasn’t looking.

You were wringing out the faintly stained towels in the kitchen sink when you heard Dean clear his throat behind you. You peered over your shoulder and shot him a smile.

“How’s he holding up?”

“Sammy’s fine, almost wouldn’t let me stitch him up,” Dean responded, shoving off from the doorway and heading over to you. “He’s passed out in the guest room now. Said he’d love a salad and a smoothie later, so I’m gonna go on a beer and burger run.”

Chuckling, you reached for a clean towel to dry off your hands. When you turned to face Dean again, he was leaning against the counter, arms crossed, eyes studying you intently. It was your turn to clear your throat as your eyes darted around the room looking for something to do.

“Y/N, I meant what I said earlier,” Dean said softly. Gaze shooting back to him and heart racing, you drew in a deep breath.

“Yeah,” you responded. “I know.”

You stared at each other for a while, Dean desperately refraining from making the first move, wanting you to come to him. After a few moments of studying his face, you could see the way he was looking at you wasn’t the heated gaze from the night before. It was different, more open and heartfelt and soft, like it had been since this morning.

Sam’s words from earlier echoed in your head.

Maybe I should give him a chance.

You drew in a deep breath. Stepping toward Dean slowly, you spoke carefully, “Okay.”

Dean blinked a few times. “Really?” he asked, voice lifting in hope. “You’re good with trying this, with… with trying us?”

You nodded, letting your own smile take over. Dean closed the space between you in one stride and, holding your face in his hands, he kissed you. His lips were soft and gentle and God you had forgotten how amazing it felt.

Dean pulled away, a giddy smile spreading across his face. “Is this where I ask you out for burgers and beer?”

You giggled, shaking your head, and reached around his neck, pulling him back in for a kiss. Your lips parted for a second and Dean was there, tugging your bottom lip between his teeth ever so gently. With a groan, you pressed yourself up against him, relishing in his warmth and firmness. Dean dropped one hand to your waist, reaching around your back to pull you closer, tilting your head with his other hand. His lips broke away, noses brushing, foreheads pressed together. You felt Dean drag in a shaky breath.

“Y/N,” he breathed before kissing you again and hoisting you up in his arms, hauling you straight to your bedroom. You wrapped yourself tightly around Dean, feeling your heart pound against his.

Once in your room, he kicked the door shut and pressed you up against it. Your feet hit the floor and Dean began pulling at your clothes, deftly popping open your jeans and sliding them down while you tore off your shirt and bra.

“Sweetheart, you don’t know what you’re doin’ to me,” he muttered, falling to his knees in front of you, his hands carefully sliding your feet out of your shoes and yanking off your jeans. His fingers ran up your legs, eyes following the trail and continuing up over your hips and breasts.

“Fuckin’ gorgeous, Y/N,” he whispered, biting his lip as he dragged your panties down to the floor. He pulled your right leg over his shoulder, gripping your ass and running his lips, his tongue, his teeth around your hips and inner thighs.

“When you were gankin’ that Wendigo today? Oh sweetheart,” he whispered. “Never seen anything like that, like you before.”

“Shit, Dean,” you breathed, resting your weight against the door. Heat flooded over you, and with a gentle sweep of his lips along the crease between your thigh and pussy, you were soaked.

“Gonna make you feel so good, Y/N.”

Your knee almost gave out as Dean’s tongue slid between your lips and began thrusting into your pussy. He groaned, resonating through you. Hands finding Dean’s head, hips riding his mouth, you let out a moan.

Dean let you ride it out, pushing his tongue deep, nose pressing against your clit. When your thrusts became erratic, Dean pinned your hips against the door, his rough hands splayed out over your soft skin, gripping tight. His tongue sought out your clit, pressing and flicking and sucking and driving you into an orgasm.

Breathing heavily, you rested your hands on Dean’s shoulders as he rose from his knees, kissing his way up to your lips, muttering praises under his breath. The taste of Dean’s sweat mingled with your wetness was erotic, and you both groaned into the kiss, all tongue and teeth and gasps.

Dean pulled away, guiding you to sit down on the bed. You yanked at the belt loops on his jeans, so he stood directly between your legs.

“Let’s get these off, hmm?” you teased, brushing your hand over his length through his jeans. Dean let out a grunt, and yanked off his shirt while you worked off his jeans and underwear. Finally, he stood naked in front of you, muscles glistening with sweat, cock out and rock hard.

You reached for him, immediately pulling his length into your mouth. Dean ran his fingers through your hair, profanities spilling from his lips, his jaw clenching when he let out a grunt. He let you take control, head bobbing as you pumped his cock.

“Fuckin’ hell, Y/N,” he gasped, pulling away. “Lay down, sweetheart.”

You laid back, watching Dean search through your drawer and slide on a condom. He turned, taking you in, all spread out for him on the bed. Your pussy clenched from his gaze, and you bit your lip, stifling a whimper in your throat.

Dean joined you on the bed, lying next to you, and you hiked your leg over his hip to straddle him. He stroked your clit and dipped in a finger, drawing out a breathy gasp from you. Raising the soaked finger to his lips, he sucked it into his mouth, relishing in your taste.

You reached down, grabbed Dean’s cock, and guided it to your entrance. Pushing him into you, you let a high whine escaped your throat. Dean rested his hands on your hips, yours on his chest for support.

Sinking fully onto him, you began a steady rhythm, Dean meeting your thrusts and stroking your hips and waist. You climbed higher, chasing your orgasm and clenching around Dean to spur on his. You felt Dean swell and he cursed, gripping your hips hard, fucking up into you, careening you into your orgasm. You fell into Dean shuddering, burying your face in the crook of his neck as you let go, Dean losing control of his thrusts as he came with you.   
When you came down, the Winchester was stroking your back and planting kisses on your head. “Hey.”

“Hey,” you murmured, propping yourself up with a smile to look him in the eyes. They were sparkling, crinkling in the corners as he grinned at you. “Those burgers are sounding pretty good right now.”

Dean’s laugh echoed throughout your room, his chest rumbling beneath you. Watching Dean, feeling your own face glowing in happiness, you decided that maybe mixing business with pleasure wasn’t that bad after all.


End file.
